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Details

Stereochemistry ACHIRAL
Molecular Formula C11H14N2O4
Molecular Weight 238.2403
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of FELBAMATE

SMILES

c1ccc(cc1)C(COC(=N)O)COC(=N)O

InChI

InChIKey=WKGXYQFOCVYPAC-UHFFFAOYSA-N
InChI=1S/C11H14N2O4/c12-10(14)16-6-9(7-17-11(13)15)8-4-2-1-3-5-8/h1-5,9H,6-7H2,(H2,12,14)(H2,13,15)

HIDE SMILES / InChI

Description
Curator's Comment:: https://www.drugs.com/cdi/felbamate.html and https://www.ncbi.nlm.nih.gov/pubmed/8383742

Felbamate is an antiepileptic indicated as monotherapy or as an adjunct to other anticonvulsants for the treatment of partial seizures resulting from epilepsy. Receptor-binding studies in vitro indicate that felbamate has weak inhibitory effects on GABA-receptor binding, benzodiazepine receptor binding, and is devoid of activity at the MK-801 receptor binding site of the NMDA receptor-ionophore complex. However, felbamate does interact as an antagonist at the strychnine-insensitive glycine recognition site of the NMDA receptor-ionophore complex. The mechanism by which felbamate exerts its anticonvulsant activity is unknown, but in animal test systems designed to detect anticonvulsant activity, felbamate has properties in common with other marketed anticonvulsants. In vitro receptor binding studies suggest that felbamate may be an antagonist at the strychnine-insensitive glycine-recognition site of the N-methyl-D-aspartate (NMDA) receptor-ionophore complex. Antagonism of the NMDA receptor glycine binding site may block the effects of the excitatory amino acids and suppress seizure activity. Animal studies indicate that felbamate may increase the seizure threshold and may decrease seizure spread. It is also indicated that felbamate has weak inhibitory effects on GABA-receptor binding, benzodiazepine receptor binding. Felbamate should be used only in those patients who respond inadequately to alternative treatments and whose epilepsy is so severe that a substantial risk of aplastic anemia and/or liver failure is deemed acceptable in light of the benefits conferred by its use. Felbatol is the brand name used in the United States for felbamate.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
0.520000000000000018 mM [IC50]
2.02000000000000002 mM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
FELBATOL

Approved Use

Not indicated as a first line antiepileptic treatment (see WARNINGS). Recommended for use only in those patients who respond inadequately to alternative treatments and whose epilepsy is so severe that a substantial risk of aplastic anemia and/or liver failure is deemed acceptable in light of the benefits conferred by its use. If these criteria are met and the patient has been fully advised of the risk, and has provided written acknowledgment, Felbamate tablets can be considered for either monotherapy or adjunctive therapy in the treatment of partial seizures, with and without generalization, in adults with epilepsy and as adjunctive therapy in the treatment of partial and generalized seizures associated with Lennox-Gastaut syndrome in children.

Launch Date

743817600000
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
14.2 μg/mL
1200 mg single, oral
dose: 1200 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
FELBAMATE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
49 μg/mL
45 mg/kg 1 times / day steady-state, oral
dose: 45 mg/kg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
FELBAMATE plasma
Homo sapiens
population: UNKNOWN
age: CHILD
sex: UNKNOWN
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
526 μg × h/mL
1200 mg single, oral
dose: 1200 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
FELBAMATE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
19.2 h
1200 mg single, oral
dose: 1200 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
FELBAMATE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
20 h
45 mg/kg 1 times / day steady-state, oral
dose: 45 mg/kg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
FELBAMATE plasma
Homo sapiens
population: UNKNOWN
age: CHILD
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
1200 mg 3 times / day steady, oral
Highest studied dose
Dose: 1200 mg, 3 times / day
Route: oral
Route: steady
Dose: 1200 mg, 3 times / day
Sources:
unhealthy, 30 years (range: 18-45 years)
Health Status: unhealthy
Age Group: 30 years (range: 18-45 years)
Sex: F
Sources:
Other AEs: Headache, Nausea...
Other AEs:
Headache (1 patient)
Nausea (5 patients)
Anorexia (3 patients)
Dyspepsia (1 patient)
Insomnia (1 patient)
Sources:
1200 mg 3 times / day multiple, oral
Recommended
Dose: 1200 mg, 3 times / day
Route: oral
Route: multiple
Dose: 1200 mg, 3 times / day
Sources:
unhealthy, adult
Other AEs: Fatigue, Weight decrease...
Other AEs:
Fatigue (6.9%)
Weight decrease (3.4%)
Face edema (3.4%)
Insomnia (8.6%)
Headache (6.9%)
Anxiety (5.2%)
Acne (3.4%)
Rash (3.4%)
Dyspepsia (8.6%)
Vomiting (8.6%)
Constipation (6.9%)
Diarrhea (5.2%)
SGPT increased (5.2%)
Hypophosphatemia (3.4%)
Upper respiratory tract infection (8.6%)
Rhinitis (6.9%)
Diplopia (3.4%)
Otitis media (3.4%)
Bleeding intermenstrual (3.4%)
Urinary tract infection (3.4%)
Sources:
AEs

AEs

AESignificanceDosePopulation
Dyspepsia 1 patient
1200 mg 3 times / day steady, oral
Highest studied dose
Dose: 1200 mg, 3 times / day
Route: oral
Route: steady
Dose: 1200 mg, 3 times / day
Sources:
unhealthy, 30 years (range: 18-45 years)
Health Status: unhealthy
Age Group: 30 years (range: 18-45 years)
Sex: F
Sources:
Headache 1 patient
1200 mg 3 times / day steady, oral
Highest studied dose
Dose: 1200 mg, 3 times / day
Route: oral
Route: steady
Dose: 1200 mg, 3 times / day
Sources:
unhealthy, 30 years (range: 18-45 years)
Health Status: unhealthy
Age Group: 30 years (range: 18-45 years)
Sex: F
Sources:
Insomnia 1 patient
1200 mg 3 times / day steady, oral
Highest studied dose
Dose: 1200 mg, 3 times / day
Route: oral
Route: steady
Dose: 1200 mg, 3 times / day
Sources:
unhealthy, 30 years (range: 18-45 years)
Health Status: unhealthy
Age Group: 30 years (range: 18-45 years)
Sex: F
Sources:
Anorexia 3 patients
1200 mg 3 times / day steady, oral
Highest studied dose
Dose: 1200 mg, 3 times / day
Route: oral
Route: steady
Dose: 1200 mg, 3 times / day
Sources:
unhealthy, 30 years (range: 18-45 years)
Health Status: unhealthy
Age Group: 30 years (range: 18-45 years)
Sex: F
Sources:
Nausea 5 patients
1200 mg 3 times / day steady, oral
Highest studied dose
Dose: 1200 mg, 3 times / day
Route: oral
Route: steady
Dose: 1200 mg, 3 times / day
Sources:
unhealthy, 30 years (range: 18-45 years)
Health Status: unhealthy
Age Group: 30 years (range: 18-45 years)
Sex: F
Sources:
Acne 3.4%
1200 mg 3 times / day multiple, oral
Recommended
Dose: 1200 mg, 3 times / day
Route: oral
Route: multiple
Dose: 1200 mg, 3 times / day
Sources:
unhealthy, adult
Bleeding intermenstrual 3.4%
1200 mg 3 times / day multiple, oral
Recommended
Dose: 1200 mg, 3 times / day
Route: oral
Route: multiple
Dose: 1200 mg, 3 times / day
Sources:
unhealthy, adult
Diplopia 3.4%
1200 mg 3 times / day multiple, oral
Recommended
Dose: 1200 mg, 3 times / day
Route: oral
Route: multiple
Dose: 1200 mg, 3 times / day
Sources:
unhealthy, adult
Face edema 3.4%
1200 mg 3 times / day multiple, oral
Recommended
Dose: 1200 mg, 3 times / day
Route: oral
Route: multiple
Dose: 1200 mg, 3 times / day
Sources:
unhealthy, adult
Hypophosphatemia 3.4%
1200 mg 3 times / day multiple, oral
Recommended
Dose: 1200 mg, 3 times / day
Route: oral
Route: multiple
Dose: 1200 mg, 3 times / day
Sources:
unhealthy, adult
Otitis media 3.4%
1200 mg 3 times / day multiple, oral
Recommended
Dose: 1200 mg, 3 times / day
Route: oral
Route: multiple
Dose: 1200 mg, 3 times / day
Sources:
unhealthy, adult
Rash 3.4%
1200 mg 3 times / day multiple, oral
Recommended
Dose: 1200 mg, 3 times / day
Route: oral
Route: multiple
Dose: 1200 mg, 3 times / day
Sources:
unhealthy, adult
Urinary tract infection 3.4%
1200 mg 3 times / day multiple, oral
Recommended
Dose: 1200 mg, 3 times / day
Route: oral
Route: multiple
Dose: 1200 mg, 3 times / day
Sources:
unhealthy, adult
Weight decrease 3.4%
1200 mg 3 times / day multiple, oral
Recommended
Dose: 1200 mg, 3 times / day
Route: oral
Route: multiple
Dose: 1200 mg, 3 times / day
Sources:
unhealthy, adult
Anxiety 5.2%
1200 mg 3 times / day multiple, oral
Recommended
Dose: 1200 mg, 3 times / day
Route: oral
Route: multiple
Dose: 1200 mg, 3 times / day
Sources:
unhealthy, adult
Diarrhea 5.2%
1200 mg 3 times / day multiple, oral
Recommended
Dose: 1200 mg, 3 times / day
Route: oral
Route: multiple
Dose: 1200 mg, 3 times / day
Sources:
unhealthy, adult
SGPT increased 5.2%
1200 mg 3 times / day multiple, oral
Recommended
Dose: 1200 mg, 3 times / day
Route: oral
Route: multiple
Dose: 1200 mg, 3 times / day
Sources:
unhealthy, adult
Constipation 6.9%
1200 mg 3 times / day multiple, oral
Recommended
Dose: 1200 mg, 3 times / day
Route: oral
Route: multiple
Dose: 1200 mg, 3 times / day
Sources:
unhealthy, adult
Fatigue 6.9%
1200 mg 3 times / day multiple, oral
Recommended
Dose: 1200 mg, 3 times / day
Route: oral
Route: multiple
Dose: 1200 mg, 3 times / day
Sources:
unhealthy, adult
Headache 6.9%
1200 mg 3 times / day multiple, oral
Recommended
Dose: 1200 mg, 3 times / day
Route: oral
Route: multiple
Dose: 1200 mg, 3 times / day
Sources:
unhealthy, adult
Rhinitis 6.9%
1200 mg 3 times / day multiple, oral
Recommended
Dose: 1200 mg, 3 times / day
Route: oral
Route: multiple
Dose: 1200 mg, 3 times / day
Sources:
unhealthy, adult
Dyspepsia 8.6%
1200 mg 3 times / day multiple, oral
Recommended
Dose: 1200 mg, 3 times / day
Route: oral
Route: multiple
Dose: 1200 mg, 3 times / day
Sources:
unhealthy, adult
Insomnia 8.6%
1200 mg 3 times / day multiple, oral
Recommended
Dose: 1200 mg, 3 times / day
Route: oral
Route: multiple
Dose: 1200 mg, 3 times / day
Sources:
unhealthy, adult
Upper respiratory tract infection 8.6%
1200 mg 3 times / day multiple, oral
Recommended
Dose: 1200 mg, 3 times / day
Route: oral
Route: multiple
Dose: 1200 mg, 3 times / day
Sources:
unhealthy, adult
Vomiting 8.6%
1200 mg 3 times / day multiple, oral
Recommended
Dose: 1200 mg, 3 times / day
Route: oral
Route: multiple
Dose: 1200 mg, 3 times / day
Sources:
unhealthy, adult
Overview

Overview

OverviewOther

Other InhibitorOther SubstrateOther Inducer







Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
likely
yes (co-administration study)
Comment: Felbamate reduced mean gestodene AUCO-24h by -42% compared with baseline, while a minor decrease (-13%), which was not assessed to be clinically relevant, was observed in ethinyl estradiol AUCO-24h
Page: 7
no
no
no
slight
yes [Inhibition 1 uM]
yes [Ki 225 uM]
weak (co-administration study)
Comment: AUCtao of phenytoin (substrate) increased by 30% when given Felbamate (1200 mg/day)
Page: 6
yes
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
likely
yes
yes
weak (co-administration study)
Comment: Carbamazepine and phenytoin increased felbamate apparent clearance by 32 to 38% relative to monotherapy
PubMed

PubMed

TitleDatePubMed
Felbamate, a novel antiepileptic agent, does not affect cognition in rodents.
1994 Jun
A self-complementary, self-assembling microsphere system: application for intravenous delivery of the antiepileptic and neuroprotectant compound felbamate.
2000 Jul
Treatment of partial seizures and seizure-like activity with felbamate in six dogs.
2001 Aug
The chemistry, toxicology, and identification in rat and human urine of 4-hydroxy-5-phenyl-1,3-oxazaperhydroin-2-one: a reactive metabolite in felbamate bioactivation.
2001 Aug
[Antiepileptic drugs and neuropathic pain].
2001 Feb 16-28
The role of new antiepileptic drugs.
2001 Jul
Advances in the treatment of epilepsy.
2001 Jul 1
Influence of retigabine on the anticonvulsant activity of some antiepileptic drugs against audiogenic seizures in DBA/2 mice.
2001 Mar
Role of glutathione S-transferases A1-1, M1-1, and P1-1 in the detoxification of 2-phenylpropenal, a reactive felbamate metabolite.
2001 May
The NMDA receptor complex: a promising target for novel antiepileptic strategies.
2001 Sep
Antiepileptic drug therapy for adults: when to initiate and how to choose.
2002 Dec
Interaction between human serum albumin and the felbamate metabolites 4-Hydroxy-5-phenyl-[1,3]oxazinan-2-one and 2-phenylpropenal.
2002 Jun
Some common issues in the use of antiepileptic drugs.
2002 Mar
Medical treatment of patients with infantile spasms.
2002 Mar-Apr
New antiepileptic drug therapies.
2002 Nov
Selection criteria for the clinical use of the newer antiepileptic drugs.
2003
Influence of felbamate on the antinociceptive action of morphine, metamizol and indomethacin in mice.
2003 May-Jun
Preclinical profile of combinations of some second-generation antiepileptic drugs: an isobolographic analysis.
2004 Aug
The new antiepileptic drugs: scientific review.
2004 Feb 4
Pharmacodynamic interaction studies with topiramate in the pentylenetetrazol and maximal electroshock seizure models.
2004 Jul
[Treatment protocol for long-term anti-epilepsy drugs in adults with refractory partial epilepsy].
2004 Jun
Effect of felbamate and its combinations with conventional antiepileptics in amygdala-kindled rats.
2004 May
Patents

Sample Use Guides

In Vivo Use Guide
Adjunctive therapy: 1200 mg/day in 3-4 divided doses. The daily dose can be increased in 1200 mg increments each week as tolerated to response. Maximum daily dose: 3600 mg.
Route of Administration: Oral
In Vitro Use Guide
At concentrations of 30 to 100 nM, Felbamate produced a significant inhibition of high-voltage-activated Ca++ currents (-6/-15%). At saturating concentrations (1-3 uM), Felbamate-mediated inhibition averaged 44% in rat cortical and neostriatal neurons.
Name Type Language
FELBAMATE
HSDB   INN   MART.   MI   ORANGE BOOK   USAN   USP-RS   VANDF   WHO-DD  
INN   USAN  
Official Name English
ADD-03055
Code English
W-554
Code English
FELBAMATE [ORANGE BOOK]
Common Name English
FELBAMATE [WHO-DD]
Common Name English
FELBAMATE [USP MONOGRAPH]
Common Name English
CARBAMIC ACID 2-PHENYLTRIMETHYLENE ESTER
Common Name English
FELBAMATE [MI]
Common Name English
FELBAMATE [USP-RS]
Common Name English
2-PHENYL-1,3-PROPANEDIOL 1,3-DICARBAMATE
Common Name English
FELBAMATE [INN]
Common Name English
1,3-PROPANEDIOL, 2-PHENYL-, DICARBAMATE
Systematic Name English
FELBATOL
Brand Name English
FELBAMATE [VANDF]
Common Name English
FELBAMATE [USAN]
Common Name English
FELBAMATE [MART.]
Common Name English
TALOXA
Brand Name English
FELBAMATE [HSDB]
Common Name English
NSC-759866
Code English
Classification Tree Code System Code
LIVERTOX 401
Created by admin on Fri Jun 25 22:05:41 UTC 2021 , Edited by admin on Fri Jun 25 22:05:41 UTC 2021
NCI_THESAURUS C264
Created by admin on Fri Jun 25 22:05:41 UTC 2021 , Edited by admin on Fri Jun 25 22:05:41 UTC 2021
NDF-RT N0000008486
Created by admin on Fri Jun 25 22:05:41 UTC 2021 , Edited by admin on Fri Jun 25 22:05:41 UTC 2021
NDF-RT N0000175753
Created by admin on Fri Jun 25 22:05:41 UTC 2021 , Edited by admin on Fri Jun 25 22:05:41 UTC 2021
FDA ORPHAN DRUG 33488
Created by admin on Fri Jun 25 22:05:41 UTC 2021 , Edited by admin on Fri Jun 25 22:05:41 UTC 2021
WHO-ATC N03AX10
Created by admin on Fri Jun 25 22:05:41 UTC 2021 , Edited by admin on Fri Jun 25 22:05:41 UTC 2021
WHO-VATC QN03AX10
Created by admin on Fri Jun 25 22:05:41 UTC 2021 , Edited by admin on Fri Jun 25 22:05:41 UTC 2021
Code System Code Type Description
RXCUI
24812
Created by admin on Fri Jun 25 22:05:41 UTC 2021 , Edited by admin on Fri Jun 25 22:05:41 UTC 2021
PRIMARY RxNorm
MESH
C047360
Created by admin on Fri Jun 25 22:05:41 UTC 2021 , Edited by admin on Fri Jun 25 22:05:41 UTC 2021
PRIMARY
NCI_THESAURUS
C47530
Created by admin on Fri Jun 25 22:05:41 UTC 2021 , Edited by admin on Fri Jun 25 22:05:41 UTC 2021
PRIMARY
EPA CompTox
25451-15-4
Created by admin on Fri Jun 25 22:05:41 UTC 2021 , Edited by admin on Fri Jun 25 22:05:41 UTC 2021
PRIMARY
IUPHAR
5473
Created by admin on Fri Jun 25 22:05:41 UTC 2021 , Edited by admin on Fri Jun 25 22:05:41 UTC 2021
PRIMARY
EVMPD
SUB07526MIG
Created by admin on Fri Jun 25 22:05:41 UTC 2021 , Edited by admin on Fri Jun 25 22:05:41 UTC 2021
PRIMARY
CAS
25451-15-4
Created by admin on Fri Jun 25 22:05:41 UTC 2021 , Edited by admin on Fri Jun 25 22:05:41 UTC 2021
PRIMARY
HSDB
7525
Created by admin on Fri Jun 25 22:05:41 UTC 2021 , Edited by admin on Fri Jun 25 22:05:41 UTC 2021
PRIMARY
FDA UNII
X72RBB02N8
Created by admin on Fri Jun 25 22:05:41 UTC 2021 , Edited by admin on Fri Jun 25 22:05:41 UTC 2021
PRIMARY
WIKIPEDIA
FELBAMATE
Created by admin on Fri Jun 25 22:05:41 UTC 2021 , Edited by admin on Fri Jun 25 22:05:41 UTC 2021
PRIMARY
DRUG BANK
DB00949
Created by admin on Fri Jun 25 22:05:41 UTC 2021 , Edited by admin on Fri Jun 25 22:05:41 UTC 2021
PRIMARY
MERCK INDEX
M5254
Created by admin on Fri Jun 25 22:05:41 UTC 2021 , Edited by admin on Fri Jun 25 22:05:41 UTC 2021
PRIMARY Merck Index
LACTMED
Felbamate
Created by admin on Fri Jun 25 22:05:41 UTC 2021 , Edited by admin on Fri Jun 25 22:05:41 UTC 2021
PRIMARY
PUBCHEM
3331
Created by admin on Fri Jun 25 22:05:41 UTC 2021 , Edited by admin on Fri Jun 25 22:05:41 UTC 2021
PRIMARY
INN
5686
Created by admin on Fri Jun 25 22:05:41 UTC 2021 , Edited by admin on Fri Jun 25 22:05:41 UTC 2021
PRIMARY
DRUG CENTRAL
1140
Created by admin on Fri Jun 25 22:05:41 UTC 2021 , Edited by admin on Fri Jun 25 22:05:41 UTC 2021
PRIMARY
USP_CATALOG
1269312
Created by admin on Fri Jun 25 22:05:41 UTC 2021 , Edited by admin on Fri Jun 25 22:05:41 UTC 2021
PRIMARY USP-RS
ECHA (EC/EINECS)
247-001-4
Created by admin on Fri Jun 25 22:05:41 UTC 2021 , Edited by admin on Fri Jun 25 22:05:41 UTC 2021
PRIMARY
ChEMBL
CHEMBL1094
Created by admin on Fri Jun 25 22:05:41 UTC 2021 , Edited by admin on Fri Jun 25 22:05:41 UTC 2021
PRIMARY